# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2379960'
loop_
_audit_author_name
_audit_author_address
'Hui Jin'
;Shenyang University of Chemical Technology
China
;
_audit_update_record             
;
2024-08-27 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N4 O'
_chemical_formula_weight         268.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.6652(12)
_cell_length_b                   11.4053(12)
_cell_length_c                   22.148(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2946.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5582
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      19.68

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52590
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.536
_diffrn_reflns_theta_max         25.101
_diffrn_reflns_theta_full        25.101
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2620
_reflns_number_gt                1718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+2.6141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2229
_refine_ls_wR_factor_gt          0.1930
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0827(3) 0.2896(4) 0.31513(19) 0.0610(11) Uani 1 1 d . . . . .
C2 C 0.0588(4) 0.1670(4) 0.2902(3) 0.0905(17) Uani 1 1 d . . . . .
H2A H 0.0657 0.1104 0.3221 0.136 Uiso 1 1 calc R U . . .
H2B H 0.1132 0.1491 0.2590 0.136 Uiso 1 1 calc R U . . .
H2C H -0.0174 0.1643 0.2739 0.136 Uiso 1 1 calc R U . . .
C3 C -0.0102(4) 0.3207(8) 0.3597(3) 0.168(4) Uani 1 1 d . . . . .
H3A H -0.0040 0.2710 0.3946 0.252 Uiso 1 1 calc R U . . .
H3B H -0.0839 0.3097 0.3413 0.252 Uiso 1 1 calc R U . . .
H3C H -0.0019 0.4011 0.3718 0.252 Uiso 1 1 calc R U . . .
C4 C 0.0800(6) 0.3741(5) 0.2612(3) 0.126(3) Uani 1 1 d . . . . .
H4A H 0.0065 0.3696 0.2418 0.190 Uiso 1 1 calc R U . . .
H4B H 0.1388 0.3527 0.2329 0.190 Uiso 1 1 calc R U . . .
H4C H 0.0930 0.4527 0.2751 0.190 Uiso 1 1 calc R U . . .
C5 C 0.2005(3) 0.2993(3) 0.34467(17) 0.0484(10) Uani 1 1 d . . . . .
C6 C 0.2856(4) 0.2153(4) 0.33784(19) 0.0603(11) Uani 1 1 d . . . . .
H6 H 0.2695 0.1480 0.3158 0.072 Uiso 1 1 calc R U . . .
C7 C 0.3940(3) 0.2285(3) 0.36284(19) 0.0572(11) Uani 1 1 d . . . . .
H7 H 0.4492 0.1705 0.3577 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4189(3) 0.3275(3) 0.39518(16) 0.0450(9) Uani 1 1 d . . . . .
C9 C 0.3362(3) 0.4115(3) 0.40331(18) 0.0530(10) Uani 1 1 d . . . . .
H9 H 0.3526 0.4784 0.4257 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2292(3) 0.3970(4) 0.37851(18) 0.0555(11) Uani 1 1 d . . . . .
H10 H 0.1742 0.4548 0.3847 0.067 Uiso 1 1 calc R U . . .
C11 C 0.5861(3) 0.2726(3) 0.46018(17) 0.0477(9) Uani 1 1 d . . . . .
C12 C 0.6912(3) 0.3110(3) 0.48271(18) 0.0521(10) Uani 1 1 d . . . . .
H12 H 0.7267 0.2676 0.5130 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7441(3) 0.4103(3) 0.46187(16) 0.0443(9) Uani 1 1 d . . . . .
C14 C 0.6839(3) 0.4727(3) 0.41527(17) 0.0456(9) Uani 1 1 d . . . . .
C15 C 0.7363(3) 0.5702(4) 0.38483(19) 0.0571(11) Uani 1 1 d . . . . .
N1 N 0.5330(2) 0.3482(2) 0.41828(13) 0.0445(8) Uani 1 1 d . . . . .
N2 N 0.5825(3) 0.4445(3) 0.39557(14) 0.0484(8) Uani 1 1 d . . . . .
N3 N 0.7815(4) 0.6449(4) 0.3607(2) 0.0863(14) Uani 1 1 d . . . . .
N4 N 0.8454(3) 0.4500(3) 0.48199(14) 0.0554(9) Uani 1 1 d . . . . .
H4D H 0.8815 0.4124 0.5098 0.066 Uiso 1 1 calc R U . . .
H4E H 0.8743 0.5131 0.4671 0.066 Uiso 1 1 calc R U . . .
O1 O 0.5349(2) 0.1806(2) 0.47389(13) 0.0630(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.509(7) . ?
C1 C5 1.526(5) . ?
C1 C2 1.529(6) . ?
C1 C4 1.535(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C10 1.384(5) . ?
C5 C6 1.389(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(5) . ?
C8 N1 1.446(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.246(4) . ?
C11 C12 1.394(5) . ?
C11 N1 1.410(5) . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 N4 1.342(4) . ?
C13 C14 1.437(5) . ?
C14 N2 1.301(4) . ?
C14 C15 1.437(5) . ?
C15 N3 1.136(5) . ?
N1 N2 1.338(4) . ?
N4 H4D 0.8600 . ?
N4 H4E 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C5 110.4(4) . . ?
C3 C1 C2 108.7(5) . . ?
C5 C1 C2 112.7(4) . . ?
C3 C1 C4 110.3(5) . . ?
C5 C1 C4 107.8(4) . . ?
C2 C1 C4 106.8(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C5 C6 116.2(3) . . ?
C10 C5 C1 120.6(3) . . ?
C6 C5 C1 123.2(3) . . ?
C7 C6 C5 122.2(4) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 N1 121.0(3) . . ?
C9 C8 N1 119.1(3) . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 122.2(4) . . ?
C9 C10 H10 118.9 . . ?
C5 C10 H10 118.9 . . ?
O1 C11 C12 126.8(4) . . ?
O1 C11 N1 117.7(3) . . ?
C12 C11 N1 115.5(3) . . ?
C13 C12 C11 122.3(4) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N4 C13 C12 124.3(3) . . ?
N4 C13 C14 120.1(3) . . ?
C12 C13 C14 115.5(3) . . ?
N2 C14 C15 114.9(3) . . ?
N2 C14 C13 124.2(3) . . ?
C15 C14 C13 120.8(3) . . ?
N3 C15 C14 177.4(5) . . ?
N2 N1 C11 124.0(3) . . ?
N2 N1 C8 113.5(3) . . ?
C11 N1 C8 122.5(3) . . ?
C14 N2 N1 118.0(3) . . ?
C13 N4 H4D 120.0 . . ?
C13 N4 H4E 120.0 . . ?
H4D N4 H4E 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C5 C10 -47.3(6) . . . . ?
C2 C1 C5 C10 -169.0(4) . . . . ?
C4 C1 C5 C10 73.4(5) . . . . ?
C3 C1 C5 C6 135.2(5) . . . . ?
C2 C1 C5 C6 13.5(6) . . . . ?
C4 C1 C5 C6 -104.2(5) . . . . ?
C10 C5 C6 C7 -0.7(6) . . . . ?
C1 C5 C6 C7 177.0(4) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C6 C7 C8 N1 -175.6(3) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
N1 C8 C9 C10 175.9(3) . . . . ?
C8 C9 C10 C5 -0.3(6) . . . . ?
C6 C5 C10 C9 1.0(6) . . . . ?
C1 C5 C10 C9 -176.8(4) . . . . ?
O1 C11 C12 C13 175.7(4) . . . . ?
N1 C11 C12 C13 -5.3(5) . . . . ?
C11 C12 C13 N4 -179.6(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
N4 C13 C14 N2 -175.9(3) . . . . ?
C12 C13 C14 N2 4.4(6) . . . . ?
N4 C13 C14 C15 7.1(5) . . . . ?
C12 C13 C14 C15 -172.7(4) . . . . ?
O1 C11 N1 N2 -173.9(3) . . . . ?
C12 C11 N1 N2 7.0(5) . . . . ?
O1 C11 N1 C8 5.4(5) . . . . ?
C12 C11 N1 C8 -173.7(3) . . . . ?
C7 C8 N1 N2 117.8(4) . . . . ?
C9 C8 N1 N2 -58.9(4) . . . . ?
C7 C8 N1 C11 -61.6(5) . . . . ?
C9 C8 N1 C11 121.8(4) . . . . ?
C15 C14 N2 N1 174.3(3) . . . . ?
C13 C14 N2 N1 -3.0(5) . . . . ?
C11 N1 N2 C14 -3.0(5) . . . . ?
C8 N1 N2 C14 177.6(3) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046

